Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Detailed Action
This office action is in response to applicant’s communication filed on 5/16/2023. Claims 1-11 are pending and are being examined in this Office Action.
Priority
The applicant claims benefit as follows:
PNG
media_image1.png
178
504
media_image1.png
Greyscale
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged. Applicant has not complied with one or more conditions for receiving the benefit of an earlier filing date under 35 U.S.C. 365(c) as follows:
The later-filed application must be an application for a patent for an invention which is also disclosed in the prior application (the parent or original nonprovisional application or provisional application). The disclosure of the invention in the parent application and in the later-filed application must be sufficient to comply with the requirements of 35 U.S.C. 112(a) or the first paragraph of pre-AIA 35 U.S.C. 112, except for the best mode requirement. See Transco Products, Inc. v. Performance Contracting, Inc., 38 F.3d 551, 32 USPQ2d 1077 (Fed. Cir. 1994).
The disclosure of the prior-filed applications, EP 20208401.8, fails to provide adequate support or enablement in the manner provided by 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph for one or more claims of this application. These applications do not disclose applicant’s molar ratios and excess water added. Thus, the priority date of claims 2, 3, 10, and 11 are 11/09/2021.
Objections
Claims 1 and 4 are objected to because of the following informalities:
Claim 1 recites “Process to the compound”. The examiner recommends instead including the missing verb to recite “Process to prepare the compound”.
Claim 1 recites “wherein a first step”. The examiner recommends instead “comprising in a first step” to incorporate “comprising” transitional language.
Claim 4 recites “process is carried”. The examiner recommends for clarity instead “process is carried out”.
Appropriate correction is required.
Claim Rejections – 35 USC 102/103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of the AIA 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102 of this title, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-11 are rejected under 35 U.S.C. 102(a)(1) and /or 102(a)(2) as being anticipated by or, in the alternative under 35 U.S.C. 103(a) as being obvious over Berni Canani et al. (Berni et al. is used herein) (US 20110098319, published April 28, 2011).
The instant claims are drawn to:
PNG
media_image2.png
702
566
media_image2.png
Greyscale
Berni et al. teaches phenylalanine carboxamide (0.01 mol) reacted with butyroyl chloride (0.01 mol), which gives a molar ratio of butyroyl chloride to phenylalanine carboxamide of 1:1. The reaction is performed in 50 ml of chloroform, reacting at room temperature for 24 hours. The resulting reaction mixture was evaporated to give a solid, which was washed with 1% aqueous sodium bicarbonate solution. The aqueous sodium bicarbonate solution was extracted with ethyl acetate to give a mixture of derivative products which was further purified on a silica gel column and recrystallized to give the final compound 1, N-(1-carbamoyl-2-phenyl-ethyl)butyramide (applicant’s compound I) in equal or greater than 50% final yield (0.005 mol; MW 234) (Example 1, paragraphs 55-56).
Berni et al. teaches the equivalency of butyroyl chloride and butyric anhydride for the synthesis of the amide derivative of butyric acid with phenylalanine (which corresponds to N-(1-carbamoyl-2-phenyl-ethyl)butyramide, applicant’s compound I) from appropriate phenylalanine derivative, see Y in claim 1 in an aprotic inert organic solvent, in which Y also represents acyl (2-6 carbon atoms) in
PNG
media_image3.png
109
94
media_image3.png
Greyscale
(paragraph 27 and claim 1). The compound (I) is prepared by reacting the two compounds indicated above, preferably in substantially equimolecular amounts, in an aprotic polar inert organic solvent such as, benzene, toluene or chloroform at room temperature (paragraph 43).
Applicant’s compound (II) is specifically disclosed in Berni et al. In claim 1, Berni et al. teaches a process for producing amide derivatives by reacting a short-chain fatty acid derivative with a phenylalanine derivative as shown below:
PNG
media_image4.png
174
428
media_image4.png
Greyscale
Berni et al.’s phenylalanine derivative in claim 1 (shown above, left compound) reads on applicant’s compound (II), when X = nitrogen, R = R1 = R2 = R4 = hydrogen and W is nil.
Because Berni et al. teaches the new compounds can be synthesized by reaction of an acid halide with a naturally occurring amino acid, such as a phenylalanine derivative (abstract), this would read on L-phenylalanine, since the L form is naturally occurring. Even if it does not, it would be reasonable to use the chiral L form of the phenyalanine derivative as the reactant, since the naturally occurring form is the form that is most abundant.
Since Berni et al. does not explicitly state the pressure during the synthesis, it would be reasonable to expect the pressure to be ambient pressure (required by claim 6 and 7), since when no pressure is given in synthetic reactions, one of ordinary skill in the art would assume ambient pressure, absent evidence to the contrary. Even if it does not, it would be obvious to optimize the pressure in order to decrease impurities and increase the yield of the product during routine optimization.
Because Berni et al. teaches an aqueous sodium bicarbonate solution was added to the evaporated reaction mixture as a wash, this would read on applicant’s limitation for “water is added to the reaction mixture” in claim 1. Even if it does not, it would be reasonable to add a water-based solution to the reaction mixture in order to quench the reaction and to remove impurities, in particular water soluble impurities, along with the wash solution adjusting the pH.
Since Berni et al. teaches that the addition of the aqueous solution is used as a wash of the reaction mixture, it would be reasonable to expect that the water that is used is distilled water (required by claim 8), in order to minimize the dissolved ions in the water and to minimize the impurities in the product. It would also be reasonable to expect that the added aqueous water solution, as compared to the amino acid derivative starting material (compound II), would be added in great excess, well above a molar ratio of 5:1 for added water to compound II (required by claims 10 and 11), since the water aqueous solution is not used as a reagent but as a wash. Even if it does not, it would be obvious to optimize the molar ratio of the added water solution to compound II in order to increase the amount of impurities washed away in the aqueous sodium bicarbonate water solution.
Berni et al. teaches the excess use of 0.015 mol of butyroyl chloride with 0.01 mol of the amino acid derivative reagent, 2-amino-2-p-toluylacetamide, to synthesize the substituted product, N-(1-carbamoyl-p-toluyl-methyl)butyramide (Example 2, paragraphs 69-70).
Since Berni et al. teaches the excess use of the butyric reagent (corresponding to applicant’s compound III), as compared to the amino acid derivative reagent (corresponding to applicant’s compound II), it would be obvious to utilize a molar ratio of excess compound III to compound II of at least 2:1 (required by claims 2 and 3), especially since the butyric reagent (corresponding to applicant’s compound III) is more volatile, making any excess reagent easier to remove from the synthesized product (butyric anhydride boiling point is 198 degree C).
With regard to the water temperature of claim 9 being below 20 degree C, it would be reasonable to expect that the aqueous sodium bicarbonate solution was stored in the refrigerator, which has a temperature of approximately 3 degree C, since wash solutions are often stored in cool conditions to prevent mold, algae or contaminant growth. Even if the aqueous sodium bicarbonate solution was not below 20 degree C, it would be obvious to cool the aqueous wash solution before washing the reaction mixture in order to decrease the amount of product lost in the aqueous solution wash.
Therefore these claims are fully met.
Conclusion
Claims 1-11 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/YIH-HORNG SHIAO/Primary Examiner, Art Unit 1691